You Know the Freedom Trail — Now Try These Other Can't-Miss Things to Do in Boston

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Boston is a compact city, but it's jam-packed with stuff to do. History buffs will appreciate the city's rich colonial heritage, while culture lovers can visit top museums like the Museum of Fine Arts and the galleries in the South End. There’s also plenty of top-notch hotels and restaurants, and, of course, Red Sox baseball. If you’re heading to Boston, here are some of the best things to do.

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1Visit The Institute of Contemporary Art

Institute of Contemporary Art ​

Boston is famous for its colonial-era attractions, and if you're in town, you'll no doubt be visiting a few, but the city also has a first-rate modern-art museum. Located in a sleek glass building on the harbor in the buzzy Seaport District, The Institute of Contemporary Art is known for its large-scale installations and visual arts.

Paul Revere was a silversmith by trade, and some of his works, including a fluted teapot, are on display at the Museum of Fine Arts. You can also see colonial artwork by John Singleton Copley, including an iconic painting of the great patriot himself. The Paul Revere House, the city's oldest dwelling, is also well worth a tour.

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3Stroll Through Our Nation's Oldest City Park

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Once used as a cow pasture and a mustering ground for British soldiers, Boston Common, the country's oldest city park, dates back to 1634! Today, it's still a hub, hosting speeches, marches, and other important events. Just next door is the Public Garden, too (you're never too old to take a ride on a Swan Boat ride on the lagoon).

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4Walk the Entire Freedom Trail

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It’s free to walk the 2.5-mile Freedom Trail (keep following that red line on the pavement), where you can stop into some of nation's most historic sights, including the Old North Church, the Bunker Hill Monument, and the site of the Boston Massacre, which took place in 1770 and is known as the "powder keg that lit the Revolution."

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5Dine in a Barbara Lynch Restaurant

Menton

James Beard Award winner Barbara Lynch is one of Boston’s top chefs, and her culinary empire continues to expand. Menton, serving haute Italian-French cuisine, is one of Boston's best restaurants, but more casual options include the trattoria-inspired Sportello and The Butcher Shop for charcuterie, cheese, and wine.

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6Snap Photos of the Green Monster

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If you haven't yet seen a Red Sox game at Fenway Park, you're totally missing out. Baseball's oldest stadium — it was built in 1912 — is small, so you'll have good views from most seats. Plus, it's home to the famous Green Monster, the 37-foot-high wall in left field. Not baseball season? Take a Fenway Park tour instead.

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7Eat a Hyper-Seasonal Meal at Cultivar

Cultivar

At Cultivar, in the Ames Hotel, chef-owner Mary Dumont turns out farm-to-table dishes using hyper-seasonal ingredients from area farmers and foragers — and even from her own on-site hydroponic garden housed in a former shipping container. Expect dishes like North Star Farm lamb with smashed sunchoke and smoked carrots.

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8Pedal Around Town on a Free Loaner Bike

Kimpton Hotels

The newly renovated Kimpton Nine Zero Hotel has plenty of fun perks, including loaner bikes that you can use to tool around town (the Fens and Arnold Arboretum are top parks for cycling). It also offers yoga mats in every room, plus a complimentary European-style breakfast and afternoon wine reception in the lobby.

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9Fill Up on Italian Fare in the North End

Mike's Pastry

Boston’s oldest neighborhood is known for its touristy Italian restaurants on Hanover Street (and down its side streets). Join the lines outside Giacomo’s for chicken parm, while Panza is tops for pasta like linguine with clams. Don't forget to stop into old-school Mike's Pastry for a cannoli — there are over a dozen flavors to choose from!

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10Soak Up Skyline Views from a Rooftop Bar

Lookout Rooftop and Bar,

When the weather cooperates, head to a rooftop bar for an alfresco drink. Atop the Seaport's Envoy Hotel is the Lookout Rooftop and Bar, overlooking the harbor and serving local brews like Bent Water and Lord Lobo. Nearby is the 12th floor Sky Lounge at the new YOTEL and rooftop bar at the Revere Hotel.

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11Blow Up Your Instagram in Beacon Hill

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Beacon Hill, with its cobbled lanes and Federal-stye redbrick townhouses, is total Insta-bait. You'll definitely want to post a few pics of Acorn Street, Boston's most photographed lane, complete with window box flowers and gas lanterns. After a stroll, stop for a cappuccino and a pecan tart at Tatte Bakery on Charles Street.

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12Slurp Super Fresh Oysters

Morgan Ione Yeager Photography

Oyster lovers won't be lacking for choice in Boston! The Seaport's trendy Row 34 and sister spot Island Creek Oyster Bar both have plenty of locally sourced bivalves. Barbara Lynch's B&G Oysters in the South End is another standout (try the fried oysters), as is Neptune Oyster, an upscale oyster bar in the North End (the lobster rolls rock, too).

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13Spend the Night in the Slammer

The Liberty Hotel

Ever wonder what it's like to spend a night in the slammer? Wearing a Yankees T-shirt might land you there, but otherwise, you can stay at The Liberty, a luxury hotel in the city's former jail. Have a drink in the lobby atrium, featuring revamped metal catwalks and original exposed brick, or in Alibi, set in the jail's former drunk tank.

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14Tour Old Ironsides in the Navy Yard

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Take a tour of the USS Constitution, aka Old Ironsides, which takes pride of place in the Charlestown Navy Yard on the Charles River. The wooden-hulled, three-masted frigate, launched in 1797, defeated five British warships during the War of 1812. While you're in Charleston, stop into the historic Warren Tavern for a pint.

A fun amenity during a stay at the swanky Langham, in the former Federal Reserve Bank building, is taking a chauffeured ride in its house car, a pink English-style taxi (free for guests). But with its elegant rooms, afternoon tea, and the recently revamped Bond Restaurant and Lounge, it might be tempting to simply stay put.

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17Go Gallery Hopping in the South End

SoWa Open Market

South End's SoWa (South of Washington) is one of the country's leading art and design districts. Browse in Boston Sculptors Gallery, Abigail Ogilvy Gallery, Laconia Gallery, and others, and on Sundays, spend a few hours at the popular SoWa Open Market (May through mid-October), featuring artists, farmers, and brewers.

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18Explore Cambridge Across the Charles River

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Harvard and MIT are located here, and a visit to their campuses is worthwhile (both offer self-guided walking tours). You can also grab lunch at places like Little Donkey, a trendy tapas bar. Nearby in hipster Somerville, a stop at Union Square Donuts is a must — you can't go wrong with the toasted coconut or Boston cream.

For an action-packed day trip, Boston Harbor Cruises' high-speed catamaran ferry will get you from Boston's Long Wharf to Provincetown at the tip of Cape Cod in just 90 minutes (offered from mid-May until early October). If you'd rather stick to the harbor area, sign up for the 90-minute sunset sightseeing cruise.

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Jill FergusTravel EditorJill has been the travel editor at BestProducts.com since 2017, showing her expertise on everything from the Best Rooftop Bars in NYC to the 30 Most Beautiful Cities in the World; the NYC native has previously worked at Travel & Leisure and has written articles for The New York Times, InStyle, Huffington Post, and Fodors.